diff --git a/InvenTree/InvenTree/settings.py b/InvenTree/InvenTree/settings.py
index 279225355d..9688f90c12 100644
--- a/InvenTree/InvenTree/settings.py
+++ b/InvenTree/InvenTree/settings.py
@@ -900,3 +900,4 @@ if DEBUG or TESTING:
 PLUGIN_TESTING = get_setting('PLUGIN_TESTING', TESTING)  # are plugins beeing tested?
 PLUGIN_TESTING_SETUP = get_setting('PLUGIN_TESTING_SETUP', False)  # load plugins from setup hooks in testing?
 PLUGIN_RETRY = get_setting('PLUGIN_RETRY', 5)  # how often should plugin loading be tried?
+PLUGIN_FILE_CHECKED = False                    # Was the plugin file checked?
diff --git a/InvenTree/common/models.py b/InvenTree/common/models.py
index 56e41dd24b..1a9b6f37d4 100644
--- a/InvenTree/common/models.py
+++ b/InvenTree/common/models.py
@@ -1007,6 +1007,13 @@ class InvenTreeSetting(BaseInvenTreeSetting):
             'validator': bool,
         },
 
+        'PLUGIN_ON_STARTUP': {
+            'name': _('Check plugins on startup'),
+            'description': _('Check that all plugins are installed on startup - enable in container enviroments'),
+            'default': False,
+            'validator': bool,
+            'requires_restart': True,
+        },
         # Settings for plugin mixin features
         'ENABLE_PLUGINS_URL': {
             'name': _('Enable URL integration'),
diff --git a/InvenTree/plugin/apps.py b/InvenTree/plugin/apps.py
index 75063c6b3c..c611f6f8c1 100644
--- a/InvenTree/plugin/apps.py
+++ b/InvenTree/plugin/apps.py
@@ -30,6 +30,15 @@ class PluginAppConfig(AppConfig):
 
                 if not registry.is_loading:
                     # this is the first startup
+                    try:
+                        from common.models import InvenTreeSetting
+                        if InvenTreeSetting.get_setting('PLUGIN_ON_STARTUP', create=False):
+                            # make sure all plugins are installed
+                            registry.install_plugin_file()
+                    except:
+                        pass
+
+                    # get plugins and init them
                     registry.collect_plugins()
                     registry.load_plugins()
 
diff --git a/InvenTree/plugin/registry.py b/InvenTree/plugin/registry.py
index 928f238f58..2db1beb805 100644
--- a/InvenTree/plugin/registry.py
+++ b/InvenTree/plugin/registry.py
@@ -8,6 +8,8 @@ Registry for loading and managing multiple plugins at run-time
 import importlib
 import pathlib
 import logging
+import os
+import subprocess
 from typing import OrderedDict
 from importlib import reload
 
@@ -211,6 +213,27 @@ class PluginsRegistry:
         # Log collected plugins
         logger.info(f'Collected {len(self.plugin_modules)} plugins!')
         logger.info(", ".join([a.__module__ for a in self.plugin_modules]))
+
+    def install_plugin_file(self):
+        """
+        Make sure all plugins are installed in the current enviroment
+        """
+
+        if settings.PLUGIN_FILE_CHECKED:
+            logger.info('Plugin file was already checked')
+            return
+
+        try:
+            output = str(subprocess.check_output(['pip', 'install', '-U', '-r', settings.PLUGIN_FILE], cwd=os.path.dirname(settings.BASE_DIR)), 'utf-8')
+        except subprocess.CalledProcessError as error:  # pragma: no cover
+            logger.error(f'Ran into error while trying to install plugins!\n{str(error)}')
+            return False
+
+        logger.info(f'plugin requirements were run\n{output}')
+
+        # do not run again
+        settings.PLUGIN_FILE_CHECKED = True
+
     # endregion
 
     # region registry functions
diff --git a/InvenTree/plugin/serializers.py b/InvenTree/plugin/serializers.py
index 14c2c11ec6..6965f398f0 100644
--- a/InvenTree/plugin/serializers.py
+++ b/InvenTree/plugin/serializers.py
@@ -16,7 +16,6 @@ from django.utils import timezone
 from rest_framework import serializers
 
 from plugin.models import PluginConfig, PluginSetting
-from InvenTree.config import get_plugin_file
 from common.serializers import SettingsSerializer
 
 
@@ -123,7 +122,7 @@ class PluginConfigInstallSerializer(serializers.Serializer):
 
         # save plugin to plugin_file if installed successfull
         if success:
-            with open(get_plugin_file(), "a") as plugin_file:
+            with open(settings.PLUGIN_FILE, "a") as plugin_file:
                 plugin_file.write(f'{" ".join(install_name)}  # Installed {timezone.now()} by {str(self.context["request"].user)}\n')
 
         return ret